America: Conquerer of the Global Menswear Market

As the label suggests, Band of Outsiders, Scott Sternberg's Los Angeles-based company, was founded on rebellious values. But the designer's über-chic aesthetic could hardly be called renegade. He favors the nattily elegant look of Brooks Brothers classics—khakis, trench coats, double-breasted jackets—seen through ironic eyes.

"I knew I wanted to be part of the cultural dialogue somehow," says Sternberg, 33, a former CAA agent and self-described clotheshorse and geek. "Like a cinephile knows about film, I know about clothes." With no fashion training other than his shopping habit, he opened his company almost five years ago, hoping to make the kind of classic but twisted clothes he favors. "I don't relate to a slick European sensibility, and I don't wear a lot of black," Sternberg says. Instead, Band of Outsiders' signatures tend toward shrunken prep-school blazers and Jacquard ties.

The designer sees his work as a response to big American fashion brands. "These are classic styles that have been around forever, only I subvert them," Sternberg says. He skews the proportions of jackets and overdyes otherwise classic button-downs, often printing them with cliché motifs in a haphazard way. "What Ralph Lauren does is brilliant. But it's a fantasy of being a Wasp or rich. I address these clichés. It's postmodern," says Sternberg, whose spring collection was based on 1950s photographs of his grandfather in Havana. Still, he admits, "squint your eyes, and it's all the same khakis and oxford-cloth shirt." His long-term aim for the label is to keep it personal. "I want to create a really big brand that feels like a small brand," he says.